4-Bromo-N-[(5S,5aS,8aR,9R)-8-oxo-9-(3,4,5-trimethoxy-phenyl)-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl]-benzamide

ID: ALA2270930

Chembl Id: CHEMBL2270930

PubChem CID: 76319716

Max Phase: Preclinical

Molecular Formula: C29H26BrNO8

Molecular Weight: 596.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc([C@@H]2c3cc4c(cc3[C@@H](NC(=O)c3ccc(Br)cc3)[C@H]3COC(=O)[C@H]23)OCO4)cc(OC)c1OC

Standard InChI:  InChI=1S/C29H26BrNO8/c1-34-22-8-15(9-23(35-2)27(22)36-3)24-17-10-20-21(39-13-38-20)11-18(17)26(19-12-37-29(33)25(19)24)31-28(32)14-4-6-16(30)7-5-14/h4-11,19,24-26H,12-13H2,1-3H3,(H,31,32)/t19-,24+,25-,26+/m0/s1

Standard InChI Key:  WIKOJTDPEBSJCK-QNMIOERPSA-N

Alternative Forms

1. Parent:

   

   ALA2270930

   N-[(5S,5aS,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-5-yl]-4-bromobenzamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 596.43

Molecular Weight (Monoisotopic): 595.0842

AlogP: 4.61

#Rotatable Bonds: 6

Polar Surface Area: 101.55

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa:

CX Basic pKa:

CX LogP: 3.96

CX LogD: 3.96

Aromatic Rings: 3

Heavy Atoms: 39

QED Weighted: 0.41

Np Likeness Score: 0.70

References

1. Xu H, Zhang X, Tian X, Lu M, Wang YG..  (2002)  Synthesis and insecticidal activity of novel 4beta-halogenated benzoylamino podophyllotoxins against Pieris rapae Linnaeus.,  50  (3): [PMID:11911206] [10.1248/cpb.50.399]

Source

Source(1):

• Scientific Literature